The concept of green chemistry has been globally adopted to improve human health and environment. As a part of our ongoing research to develop greener methodologies, targeted to the synthesis of medicinally significant molecules, an ecofriendly method has been developed to synthesize bioactive pyrroles following Clauson-kaas strategy.This newly developed method involves tomato juice as green solvent and catalyst and microwave irradiation as green energy source. <i>Solanum lycopersicum</i> or Roma tomato is one of the cheapest vegetables and its juice contains approximately 10 organic acids out of which citric, malic, and ascorbic acids are prevailing. Tomato juice has been used as a solvent whereas the Brφnsted acids present therein catalyze the reaction. In other words, the double role of tomato juice, as solvent and catalyst, has been explored. In the presence of microwave irradiation, the water present in the juice should play the role of an ideal polar solvent and the organic acids present therein catalyzed the reaction. A wide variety of diversely substituted amines have been used to accomplish a series of pyrrole derivatives. The high yields of the desired products confirm that tomato juice is able to play the dual role as solvent as well as catalyst. Some of these pyrrole derivatives demonstrated potential anticancer activity. The method reported herein satisfies many principles of green chemistry by replacing hazardous solvents, catalysts, and solid supports, retaining atom economy and shortening reaction time. This newly developed methodology should provide a valid contribution to the existing processes in the same field from environmental viewpoint. To the best of our knowledge, this is the first report of replacement of organic solvent and catalyst by tomato juice in chemical laboratory to accomplish the synthesis of medicinally privileged molecules.

Nexus of food, energy, and bioactivity: Tomato juice mediated, microwave-assisted green route towards bioactive pyrroles

255th National Meeting (2018)

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